He Did It His Way: All the (Many) Women in Frank Sinatra’s Life

We can say a lot of thing about Ole’ Blue Eyes, like how he’s the original “swinger,” the world’s greatest crooner, an Oscar-winning actor, a drinker, a manic/depressive, an insomniac, and the leader of the Rat Pack. Oh, and let’s not forget: a ladies’ man. Frank Sinatra certainly loved women, and they certainly loved him. And what wasn’t to love? He was good-looking, charming, talented, and had the voice of a god.

According to Sinatra’s friend Joey D’Orazio, the crooner once confided to him: “I just want to make it with as many women as I can.” One of his go-to phrases, when he hung out with his pals in the lounge of the Sands hotel in Las Vegas, was, “We’re all men sitting there. Where are the broads?” Well, that sums it up! And let us sum it up even further while providing the full list of Sinatra’s ladies…

What He Looked for in a Woman

First, let’s ask ourselves, what did Frank Sinatra look for in a woman? Well, he once answered that very question with “A sense of humor.” He then added: “I’m supposed to have a Ph.D. on the subject of women, but the truth is, I’ve flunked more often than not. I’m very fond of women; I admire them. But like all men, I don’t understand them.”

Sinatra once said that the first thing he noticed about a woman was her hands. “How they’re kept,” to be exact. “Grooming is important.” He also said that he doesn’t like “excessive makeup.” According to his former valet George Jacobs, the singer “craved class.” He also hated women who smoked excessively.

How He Was on Dates

When it came to going on dates, Sinatra loved driving his ladies around himself (instead of a chauffeur). He purposely never drove Actress Angie Dickinson, one of his many girlfriends, around in a convertible because he knew she didn’t want her hair to get messed up. And when it came to dancing, according to his second wife Ava Gardner, “He was hopeless on the dance floor.”

Although his list of women, as you’ll see, is filled with beauties, he didn’t like women who tried too hard. There was one time when, out of curiosity, Sinatra went to Hugh Hefner’s Playboy Club in Chicago. He reportedly said that he thought the girls tried too hard. He even skipped out on the festivities and went back to his room at the Ambassador Hotel.

Nancy Barbato: The First Wife

Nancy Barbato Sinatra was Frank Sinatra’s first wife and the mother of his three children (Nancy Jr., Frank Jr., and Tina). Naturally, she was a comforting source of stability (with her home-cooked meals) in his life. In 2018, she died at the age of 101. The two met long, long ago, in 1934 at a summer camp (which only makes it cuter) when they were teenagers.

As Nancy was painting her nails on the porch, Frank was playing love songs on his ukulele. They married in 1939. She stayed by his side, despite knowing full well that he was cheating on her. They eventually divorced, though, in 1951. But other than being Sinatra’s wife, what do we know about the woman?

Sewing Bowties and Cooking Pasta

Mrs. Sinatra had worked as a secretary and would sew her husband’s silk bow ties during his early days when he was struggling to launch his singing career. She made him the best Italian dishes in town, despite having to skip out on the meat in her tomato sauce in order to save money.

Nancy, who was sometimes called unflattering nicknames like “Big Nancy” or “Nancy Sr.” (after the birth of her daughter Nancy in 1940), mostly stayed in the background. But as her husband became a superstar, she started to refine her wardrobe and hairstyle and had her teeth capped.

Unhappy and Unbearable

The more famous Sinatra got, the more women wanted to go to bed with him. He was evidently not too invested in covering up the evidence, either. He and Nancy separated briefly in 1946 and for good in 1950. In one of her few public comments, Nancy stated that her marriage to Sinatra “has become most unhappy and almost unbearable.”

Nancy happened to gain sympathy in inner Hollywood circles, but she kept a low profile as she raised her children. She even gave Sinatra’s valet, George Jacobs, instructions on how to make his favorite foods, like pasta, roasted peppers, scrambled-egg sandwiches, and steak.

She Never Remarried

Within a week of their divorce, to add insult to injury, Sinatra married the glamorous movie star, Ava Gardner. Still, Nancy would pick up the phone and console her ex-husband when he would call her in the middle of the night, confiding in her about his romances with women that had hit the skids.

For years, Sinatra would drop in at his wife’s home to see their children, often coming unannounced, lighting a fire, staying for a home-cooked meal, and then sleeping on the couch. Sinatra, as we know, carried on in the love department. Nancy, however, never remarried.

Lana Turner: He Had to Have Her

According to biographer J. Randy Taraborrelli, when Sinatra first saw Lana Turner in the film The Postman Always Rings Twice in 1946, he said, “I have to have her.” And he did. In a matter of minutes, he got Turner’s phone number through a mutual friend.

He even left Nancy for the star, who by then had been in more than 20 films. She was successful, rich, and a divorcée. Sinatra later said he’d never been with a woman quite as “carnal” as Lana Turner. All she wanted to do was go to bed with him. Small talk was of no interest to her. But Sinatra eventually went back to his wife, and Turner only found out about it in the newspapers.

Judy Garland: He Was Her Rebound

Garland and Sinatra “got together” a few times over a six-year period. The first time occurred while Garland was having a breakdown; the second, during one of her divorces. It looks like Blue Eyes was Dorothy’s rebound.

It wasn’t too long ago when a love letter surfaced, written from Garland to Sinatra. The four-page handwritten note went up for bids at the RR Auction in Boston. She wrote it on her personal letterhead after a secret meeting in the Hamptons. In the letter, she wrote, “You said today that you’d been negligent. But darling, that’s so unimportant compared to the great amount of happiness you’ve given me. I shan’t forget the hours we’ve spent together — ever!”

Ava Gardner: The Second Wife (and Homewrecker)

Sinatra and Gardner were a couple for the tabloids, that’s for sure. After all, he left Nancy to marry her. It came at a time when Gardner’s career in Hollywood was just starting to take off, whereas his was beginning to fade.

The two first laid eyes on one another in 1943, reuniting in 1948 and embarking quickly into a controversial love affair. The two dated secretly for months before being spotted in 1950 having dinner together in what became their first public date. Once the cat was out of the bag, their romance was met with heavy criticism.

She Had Her Own Reputation

Gardner, who was already a Hollywood star and MGM’s hottest commodity, had a personal life that was far from simple. She was also married – to Mickey Rooney – when she sparked up a romance with Sinatra. She also had a reputation of being a serial cheater as she would go through a string of affairs and two marriages (before reaching 23) before even considering getting hitched to Frank.

Despite all the naysayers, the two just had to be together and thus risked it all. Before they even met, the singer saw a photo of Gardner and announced: “I’m going to marry that woman.”

She Was the Breadwinner

Before they got to say their vows – in fact, one day before the wedding – Gardner received a letter from a prostitute, claiming to have been sleeping with the crooner for months. Despite being overcome with jealousy and rage and doubting his faithfulness, she still walked down the aisle with him.

Their marriage didn’t settle them down, though. They became known for drinking, arguing, as well as passionately making up in public. To make matters worse, Sinatra relied on her paycheck at the end of the day as she was the breadwinner in the home.

She Ignored His Romantic Gestures

Their already turbulent marriage was put to the test when Gardner had two abortions due to the fact that she felt their union was way too unstable to provide a proper home life for a child. In 1953, she had an affair with Spain’s most popular bullfighter, Luis Miguel Dominguin.

A year later, Gardner filed for divorce. They first separated, which was the time Sinatra used to win back her love with romantic gestures, both in private and in public. But he was ultimately unsuccessful. They divorced in 1957. Gardner moved to London and, like Nancy, never remarried. She died in 1990 at the age of 67.

Angie Dickinson: The On-and-Off Girlfriend

The two were never married, but they did have an on-off relationship for 20 years. Dickinson met Sinatra in 1953 on the set of the Colgate Comedy Hour – her very first job in show business. They started dating soon after.

Dickinson appeared as Sinatra’s wife in the 1960 Rat Pack movie, Ocean’s 11, but off screen, their relationship was loose and informal. They hit it off as he was coming off of his separation with Gardner. Their love wasn’t as intense as some of his other flings. But they enjoyed each other’s company and remained friends for decades.

Lauren Bacall: The Secret Fiancée

In 1957, after her husband Humphrey Bogart died, Lauren Bacall found comfort in the arms of her longtime friend, Frank. In fact, she fell in love with him while Bogie was on his death bed with throat cancer.

She then accepted Sinatra’s marriage proposal, although he was hesitant and wanted them to keep it a secret. It was deemed a betrayal on both their parts as Sinatra basically worshipped Bogart. The tabloids, as they always do, found out about the secret engagement and spread the news. Sinatra believed it was Bacall herself who broke the news, so he left her on the spot.

Marilyn Monroe: The Seductive Roommate

Sinatra and Monroe were good friends and even lived together after they separated from each of their spouses (Ava Gardner and Joe DiMaggio). But their platonic relationship ended when he found her standing by the fridge one morning in the nude, deciding between grapefruit and orange juice.

Apparently, he proposed to her in 1961, but she turned him down. Like with most of the men in Monroe’s life, she had a complicated relationship with Ol’ Blue Eyes. Some say that Sinatra asked her to marry him because he was so intent on saving her from her demons.

Bubble Baths and Mixed Messages

The two saw each other casually in the late 1950s, including the time they briefly lived together, but their romance reached a boiling point in 1961. “They spent a lot of nights together,” said Sinatra’s friend Jimmy Whiting. “They took bubble baths together.”

Marilyn was dependent on Frank. “She used to say, ‘If I have any problem, there’s only one person I know can help: Frankie,’” Whiting recalled. He did love her, but he needed to keep his distance. Then, in 1962, he announced his engagement to dancer Juliet Prowse, which shocked even his closest friends.

He Couldn’t Save Her, but He Tried

That August, Sinatra invited Monroe to Cal-Neva Lodge in Lake Tahoe. Joe Langford, a security guard there, said that when Sinatra saw her, he was “alarmed at how depressed she seemed.” Sinatra had special meals sent to her room and worried about her well-being.

But Monroe couldn’t be saved. She died one week later of an alleged overdose. “Frank was in shock for weeks,” his valet, George Jacobs, said. He was then barred from going to her funeral by Joe DiMaggio. “I loved her too,” a distraught Frank said to a friend. “No one can say I didn’t love her too.”

Juliet Prowse: The Fleeting Fiancé

The two met during the shoot of the film Can-Can. Sinatra and Prowse announced their engagement in 1962, but according to The Guardian, Prowse was more flattered than actually in love with him and preferred to focus on her career. “And after a few drinks, he could be very difficult,” she claimed.

When Sinatra proposed to the dancer, even his closest friends thought it was a way to distract himself. “I do think it had to do with Marilyn in some way, maybe trying to break from her a little,” his fellow Rat Pack member Sammy Davis Jr. said. Sinatra’s new romance ended in just six weeks. Clearly, it wasn’t true love.

Mia Farrow: The Unlikely Third Wife

When the 21-year-old actress married the over 50-year-old star in 1966, it raised some eyebrows. Farrow was labeled Sinatra’s “unlikely” wife, which could have been due to the fact that she was a 99-pound Catholic schoolgirl-turned flower child.

For a few years during the mid-‘60s, they were one of Hollywood’s questionable couples. He called her “Angel Face” while she called him “Charlie Brown.” He wined and dined Farrow, who was younger than his oldest daughter, Nancy Jr. Farrow claimed that she lost her virginity to her short-term husband.

The Butt of Jokes

Soon enough, the couple became the butt of other people’s jokes. “I always knew Frank would end up in bed with a boy,” Gardner cracked (Farrow had that ultra-short pixie cut). Farrow’s own mother, Maureen O’Sullivan, reportedly said, “If he marries anyone, it should be me.”

Yet, saying “screw it” to all the naysayers, the two got hitched in Las Vegas on July 19, 1966. But under her frail appearance, Farrow was complicated and moody. She wasn’t intimidated by the aging legend. It didn’t take long for her to get bored with him.

She Was Too Independent for Him

Farrow was tired of Sinatra and his pals, but the straw that broke the camel’s back was her refusal to abandon her film career. Sinatra, who broke off his engagement to Prowse because she refused to become a full-time wife, wasn’t pleased with Farrow’s independence.

Still, the couple compromised and agreed that she would make “only” one film a year. Then, in 1968, Farrow’s big break happened. She scored the lead role in Rosemary’s Baby. Sinatra nearly demanded that she “ankle the film” (“ditch the project”). But she didn’t and was stunned when she was served with divorce papers on the set.

The Love of Her Life

They divorced in 1968 but remained friends over the years. Unlike his previous ex-wives, Farrow did remarry to composer/conductor André Prévin. She also had a relationship with Woody Allen, with whom Sinatra had a well-publicized dust-up with over his highly controversial relationship with Farrow’s adopted daughter, Soon-Yi Previn.

Sinatra reportedly wanted to send his mob buddies to break Allen’s legs. When Sinatra died in 1998, Farrow declared that he was the love of her life. On a random note, she remembered him as a great hand-holder. They would hold hands and look up at the stars in the desert skies together. In those moments, she “felt closer to him than I’ve ever felt to anyone in my life.”

Irene Tsu: The Young Actress

Sinatra also had a two-year romance with the much younger Shanghai-born actress, Irene Tsu. The 76-year-old got candid about their affair when promoting her book A Water Color Dream: The Many Lives of Irene Tsu. She was 29 years younger than Sinatra when they were together. She revealed that he spontaneously asked her on a first date in the California desert in 1968.

It happened during the end of his marriage to Farrow. Tsu first met Sinatra when he was in Miami shooting Tony Rome. She was in town filming one of her “wiki wiki girl” ads for Chevron.

Whisked Away to the Desert

She was sent to a networking lunch at a hotel, and when Sinatra arrived, she instantly recognized him from his voice. When he caught sight of her at a Beverly Hills private club a month later, she was called to join him for dinner at 7:30 p.m. with the instructions to “Be on time.”

Tsu recalled that she “went shopping like crazy” for the perfect outfit. Sinatra then called her to tell her, “Baby, I don’t know if you heard, but my divorce has been announced, and there’s paparazzi all over my property. I’m heading out to the desert. I want you to come with me.”

A Magical Weekend

The pair then spent “a magical weekend” in the desert before she stayed in his home “in the Pink Room,” which apparently was Mia Farrow’s. He told her: “If you don’t like the color, we can change it. Pick any color you want.” (She chose buttercup yellow.)

The actress made her movie debut in 1961 in Flower Drum Song, and by the late ‘60s, she was famous for her Chevron ads, but her fame was eclipsed by Sinatra’s. Tsu recalled that they didn’t have many deep conversations. She also remembered him living with tension and bad insomnia.

Grace Kelly: More Than Just a Co-Star

Kelly and Sinatra were both legendary seducers, the only difference is that Sinatra didn’t marry into royalty. According to biographer Wendy Leigh, she was constantly cheating on her husband, the Prince of Monaco. Among her “men on the side” were Marlon Brando, Gary Cooper, Bing Crosby, and, of course, Ol’ Blue Eyes.

The two were in a few movies together, High Society and The Philadelphia Story, but they were more than just co-stars. Sinatra went to Monaco more than once, but it was usually framed publicly as his way to support the charity work of Princess Grace of Monaco. He was also friends with Prince Ranier (Kelly’s husband).

Barbara Marx: The Fourth and Final Wife

Sinatra met Barbara Marx in 1973 when he was 58 years old. And he knew that she was the right one to spend the rest of his days with. Marx was a onetime model and Las Vegas showgirl before becoming Mrs. Sinatra.

They met in 1957 when she was working at the Riviera casino in Las Vegas. Sinatra was at the height of his fame then, and he was sitting at the bar with Dean Martin, Sammy Davis Jr. and other Rat Pack guys. That’s when he called to her: “Hey, Blondie! Come over here. Join us!”

She Didn’t Want to Deal with a “Drunk.”

Marx told the Telegraph that she just kept walking. One of the girls with her said, “Do you know who that was? That was Frank Sinatra.” But she didn’t care. She told her friend, “I don’t want to deal with drunks.” She was married to Zeppo Marx, a member of the Marx Brothers’ comedy team.

She was married to Marx when she and Sinatra (who was then three times divorced) became more than casual acquaintances. “I think anyone who met Frank Sinatra would have to have sparks,” she said in 1988. “Because he is a flirt… And there’s no way to avoid that flirtation.” By the time her divorce to Marx was final in 1973, she was already Sinatra’s official girlfriend.

Lady Blue Eyes

“Fortunately, I could match Frank drink for drink and still know what I was doing,” she wrote in her 2011 memoir, Lady Blue Eyes. Sinatra chose to propose to her by placing a diamond engagement ring in a glass of champagne. The two married in 1976, and, yes, she signed a prenuptial agreement.

In her memoir, she described him as “very romantic” and also obsessed with cleanliness. Lady Blue Eyes even managed to get Sinatra to moderate his drinking in his later years. They were married for almost 22 years – longer than his three previous marriages. She was a steadying force in his life, staying by his side when his career made a remarkable resurgence in the ‘80s and ‘90s. She passed away in 2017, at the age of 90.

Nancy Sinatra Jr.: The Eldest Daughter

There are two Sinatra ladies that aren’t romantically linked to him, and they are his daughters Nancy and Tina. But we’ll start with Nancy. For all the women on this list, Sinatra was either the love of their life or that womanizing cheat; to Nancy Jr., he was just “dad.”

The now 80-year-old remembers her dad as affectionate and caring and a man who always put his children first. Nancy Jr. said, “We always knew that when push comes to shove, he’d be there for us if there were a choice.” And when he was away, he would phone them every day. His first question: “How’s the weather?”

Quality Time with Dad

Nancy also revealed that he once told her that if he could do it all again, he never would have left her mother. She described her father’s compassionate side. For instance, Sinatra would sit at the breakfast table and read the newspaper, and Nancy Jr. recalls one particular story was about a little girl who was born with her eyes too close together.

“Dad got on the phone to his secretary Dorothy and said, ‘Dot, let’s get some information about where she is.’ Sinatra then paid the girl’s bills. That’s the side of Sinatra that perhaps not everyone was aware of. Nancy Jr., along with her brother and sister, never got to say goodbye to him when he passed away, and it’s a regret that she carries with her.

A Hurtful Regret

According to Nancy, she wasn’t even told that he was in the hospital. “I had never been so angry and hurt in my life. I got the phone call from the doctor ten minutes after Daddy died.” At 11:00 at night, the doctor called her and told her that her father had just passed. She said, “What, where is he?” She and her siblings were seven minutes from the hospital.

Apparently, her father clung to his life for 50 minutes, and at one point, he said, “Where are my children?” Nancy blames Sinatra’s then-wife Barbara. In Nancy’s opinion, it was because Barbara wanted the headline to read, “With his wife by his side.” Nancy recalls telling her father once that she didn’t think she and her siblings even existed to Barbara, to which Sinatra replied, “I think you may be right.”

Tina Sinatra: The Youngest Daughter

Sinatra’s youngest daughter, Tina, has written a memoir called My Father’s Daughter. Throughout the account of tenderness, funny stories, history, and beautiful women, Tina also includes accounts of Hollywood-childhood anecdotes, adult regrets, and a fair share of false words.

According to 72-year-old Tina, her father would have thought: “It’s a child’s prerogative to write about their parent.” Tina has claimed that she has a unique vantage point. She knows, though, that she will always get backlash for the negative information she divulged about her father’s private life.

Her Mother Tried to Stop Her

The only person who tried to stop Tina from writing the memoir was her own mother, Nancy Barbato Sinatra. And, in the end, according to Tina, her mother read the book “and loves it.” She then apologized for doubting her daughter’s judgment.

The least known of the three Sinatra children devoted much of the last few decades to preserving the Sinatra legacy. She didn’t become a singer, like Nancy Jr., and she wasn’t a namesake, like Frank Jr. She did, however, spend eight years bringing the miniseries Sinatra to fruition. Tina Sinatra is a businesswoman, film producer, and Hollywood agent, as well as a memoirist.